Yarn treating process and resulting product



I Patent Nov; 1 3, 1%45 r sac rnocnss "Y ,88,& 3

r RESULTENG Eoseph B. Dickey, Rochester, N. E, and James G lidcNally, oxvllle, Tenn, 'manKodsh vllompcny, Roch pornflon of New 3 f No Bra. Applicnfion Jan .1!

Se him-517,436

(Cl. EFL-139.5)

6 Ehlms.

As is well knownin the textile industry, themanufacture, processing and use of yarns composed of or containing organic derivatives of cellulose and similar synthetic materials give rise to numerous problems generally absent from thehandlin of natural yarns such as silk, wool,

1 cotton, and thelike. One of the chief problems encolmtered in dealing with these synthetic materials is to so lubricate or soften and, in some instances, to both lubricate and soften, the yarn in question that it will have the correct frictional characteristics, or drag, and the required flexibility for the specific purpose in view. In the handling of continuous filament yarn, for examing composition, in which the several functions are properly coordinated to accomplish the desired result is often a matter of extreme dildculty. This is due to the fact that in any given yarn conditioning compositlomwhether primarily designed for use as'a warp, filling or mttlng lubricant, or as an anti-static, all of the various components and their functions must be delicately balanced one ag the other so as to give a practical and commerciafly satisfactory yarn treatment.

Heretofore, many difl erent conditioning agents such as polyhydric alcohols and similar compounds have been suggested as ingredients of yarn conditioning formulas, generally in conjunction with mlnerahvegetable and animal oils.

It has been found in practice, however, that most of these agents and the various formulas cons.

tainlng them have certain drawbacks, among which may be mentioned too drastic solvent action on the yarn, insufllcient solvent power for ple, it is necessary to condition the material to.

reduce the tendency toward breakage of individual filaments when the yarn is subjected to mechanical strains such as are involved in pas-- sage of the yarn over rolls, guides, and other parts of the yarn-producing mechanism and in twisting, winding, reeling and similar operations.

. In the case of yarns intended for use on commercial knitting machinery, it is particularly 'ditloning of textile yarns, threads, filaments, and

important that the yarn be soft and pliable in' order that itmay conformto the contour of the needles and give a closely knit fabric free from cuts. pinholes, stitch distortion, ladderlng, misplaits and other common deiec Another problem "of major proportions presented by these synthetic yarns is their extreme tendency to pick up charges or static electricity,

especially in such operations as twisting, winding, warping, picking, carding, combing, drafting, spinning, and the like. This tendency is particularly aggravated in. the case of cutstsple fibers, since in the commercial use or such mate rial it is normally subjected to a number of extremely severe operations such as picking, cordlng, combing, etci, all of which tend to so charge the individual fibers as to make most web formation difllcult orimpoulble or to give thc'ultlmaicyarnanundesirablcunevenncu In aonietypes oryarn, ali'three of the abovemcntioned problems of lubrication; softening and anti-static treatment are pt and in any cm the mstteroi provl a conditionor solubility in the lubricants with which they are usedand a tendency to form gummy deposits on the yarn after application; Furthermore, many of the known lubricating, softening and anti-static agents are lnsufllciently soluble in water to permit satisfactory removal from the yarn by aqueous scour baths.

The present invention has as its principal object to provide an improved process for the com fibers, particularly those composed of or containing organic derivativesoi cellulose to render such materials amenable to various textile operaltions and processea'such as knittin Weaving, spinning, and the like. A iurther object is to provide an lmprovedprocess tor-the lubrication,

softening and anti-static treatment of such yarn, A still further-object is to provide a new class of yarn treating agcnts and compositions particularly adapted for the conditioning of yarns composed 01 or containing organic derivatives of cellulose and readily removable therefrom by the usual aqueous scourbsths. Aspeclnc object is to provide an improved type c! cellulose organic .deriva'tive cut staple fiber amenable to carding,

drawing, spinning, andother processing steps cusi tomarily employed in' the manuiacture of lpull I yam on the woolen, worsted, and cotton 8Y3! tems. *Other objects willsppear hereinaitcn.

These objects are accomplished by the following invention which, in its broader a:

Icularlythcse comorgsnic derivatives of cellulose, h to ul. acetate, cellulose acetate propionate, cellulose acetate butyrate and similar organic acid esters with a carboxyiic amide having the formula wherein Ac is an acyl group, R1 is a member of the group consisting of furfuryl and tetrahydrofurfuryl groups and R: is a member of the group consisting of hydrogen, alkyl, hydroxyalkyl, furfuryl andtetrahydrofurfuryl groups. The acyl group may be derived from, any aliphatic or aromatic acid. The alkyl group may be any substituted or unsubstituted alkyl.

The preparation and characteristics of this class of carboxylic amides will be more fully illustrated by the following examples and description in which we have set forth several of the preferred embodiments of our invention which are included merely for purposes of illustration and not as a limitation thereof.

Parramnon or Comourms' The compounds covered by the graphic formula given above maybe prepared, for example, by reacting an appropriate furfurylamine or tetrahydromrfurylamine with the appropriate acid :or acid chloride. The acids -,we prefer; to employ are thosetypifledbystearic, oleic, ricinoleic, palmitic,

lauric sebacic, inyristic', abietic, benzoic, naphthenic and the like.,-'I'hese.may, in1genera1, be

derived from naturally-occurring oils such as 7 olive, neats-i'oot,- cotton seed, soy'a bean, whale, io- Joba, egg, menhaden and other oils. For example,.

I may prepare nitrogen -furi'u'ryl palmityl amide by causingfurfurylamine to react with palmitic acid or palmityl chloride. Practically any amide may be similarly prepared by'proce'dures typified by those illustrated in the following-examples.

' The various furfuryl 01" tetrahydrofurfuryl- 4 amines required for the preparation of such compounds maybe'prepared in accordance with procedure already known'and described in the patent literature. For example, furiurylamine; 'difm'furylamine, tetrahydrofurfurylaniine and di-' tetrahydrofuriurylamin'emay be prepared as de- The alkoxy alkylamines may be prepared as described in o. s. Patent 2,285,419.

' Example 1.'- -N-fflrfur vl palmitul" amide Furfurylamine is treated in water with one mole oi palmityl chloride and one mole of sodium hydroxide. The product which is the N-furfuryl palmityl amide separates as a light-colored viscose oil which is removed from the reaction mixture, washed with water and dried. The product has the formula CH--CH a n H -on,-N-d C1s u 0 By following the procedure outlined in the preceding paragraph any desired carboxylic amide may be prepared by employing the various furfuryl or tetrahydrofurfurylamines. In some cases, instead of employing the acid chloride, it may be desirable to employ the acid itself or glycerides of such acids as they are found in naturally-Occuror glycerides thereof which maybe present in the oil. Thus there may be prepared a large number of various amide compounds among which may be mentioned the following:

N-furiuryl stearyl amide N-furfuryl oleyl amide N-furfuryl palmityl amide N-furfuryl naphthenyl amide N-furfuryl lauryl amide N-furfuryl decyl amide N-furfuryl ceretyl amide N-furfuryl sebacamide N-difurfuryl stearyl amide N-difurfuryl oleyl amide N-difurfuryl palmityl amide N-difurfuryl naphthenyl amide N-difurfuryl lauryl amide N-difurfuryl decyl amide N-difurfuryl ceretyl amide N-difurfuryl myrlstyl amide N-djfurfuryi abietyl amide N-difurfuryl benzoyl amide N-ditetrahydrofurfuryl benzoyl amide N -ditetrahydrofurfuryl stearyl amide N-ditetrahydrofurfuryl oleyl amide N-ditetrahydrofurfuryl lauryl amide N-ditetrahydrofurfuryl palmityl amide N'-ditetrahydrofurfuryl decyl amide N-ditetrahydroturfuryl myristyl amide N-ditetrahydrofurfuryl abietyl amide I N-ditetrahydrofurfuryl sebacylamide N-tetrahydrofurfuryl furfuryl stearyl amide N-tetrahydrofurfuryl furfurylpalmityl amide N -tetrahydrofur'furyl rurfuryllauryl amide. N-tetrahydroturfuryl furfuryl oleyl-amide "N-tetrahydrofurfuryl furfuryl ricinoleyl amide N -tetrahydrofurfury1 furfuryl naphthenyl amide- N-tetrahydrofurfuryl furfuryl benzoyl amide- N-tetrahydrofurfuryl furfuryl 'abietyl amide .N-tetrahydrofurfuryl furfuryl sebacyl amide N-tetr'ahydrofurfuryl furfuryi ceretyl amide N-tetrahydrofurfuryl methyl palmityl amide N-tetrahydrofurturyl ethyl lauryl amide scribed in U. s. Patents 2,041,926 and 2,045,574.

ring oils. If one employs olive'oil, or coconut oil, 7 for example, the acids will be present in such oils as a mixture of glycerides and the resulting furfuryl or tetrahydroi'urfuryl amides obtained will I be a mixture of amides corresponding to the acids N-tetrahydrofurfuryl butyl oleyl amide N-tetrahydrofurfuryl cyclohexylmyristyl amide N-tetrahy'drofuriuryl amyl naphthenyl amide N-tetrahydrofurfflryl phen'yl abietyl amide 'N-tetrahydrofurfuryl phenyl stearyl amide N-tetrahydrofurfuryl phenyl lauryl amide N-tetrahydrofurfuryl lauryl lauryl amide N-tetrahydrofurfurylbeta-hydroxyethyl lauryl amide N-tetrahydrofurfuryl beta-hydromethyl stearyl amide N-tetrahydrofurfuryl beta-hydroxyethyl palmityl amide N-tetrahydrofurfuryl beta-hydroxyethyl sebacyl N-iurfuryl ethyloleyl amide I N-furiuryl ethyl benzoyl amide N-furfuryl butyl naphthenyl amide N-furfuryl amyl palmityl amide N-furfuryl cyclohexyl stearyl amide 'N-furfuryl phenyl stearyl amide N-furfuryl phenyl palmityl amide N-furfuryl phenyl ricinoleyl amide N-furfuryl lauryl ricinoleyl amide N-iurfuryl lauryl oleyl amide N-turi'uryl lauryl 'palmityl amide N-furfuryl lauryl naphthenyl amide N-furfuryl cetyl naphthenyl amide Example 2 In general, the primary and secondary amines are caused to form amides of ricinoleic acid by heating the acid or its methyl ester with the amine, or by using castor oil, as follows. One mole of difurfurylamine is heated at IOU-150 with one mole of methyl ricinoleate. The reaction is preferably carried out in the absence of oxygen or in the presence of an inert gas such asv nitrogen. As the reaction proceeds methanol is distilled oil? and when no more methanol is formed, the reaction is completed. The product,

which is a light yellow, heavy viscose oil iswashed with water and dried. The product is suficiently pure for use as an ingredient of a textile yarn treating composition. The product thus prepared is difurfuryLricinoleyl amide and has the graphic formula t Example 3 A mixture of the amides of the various acids present in naturally-occurring oils, such as olive, neats-foot, teaseed, whale, cotton seed, soyabean, eg menhaden and other oils, may be prepared in a manner analogous to that described in Examples 1 and 2, that is, by heating the oil, preferably in the absence of oxygen, to a temperature of IOU-150 C. For example, one mole of tetrahydrofurfurylamine is mixed with 500 grams of olive oil andheated to a temperature of 150-175 for a period of about two hours. The product which is a heavy, viscous, colorless oil is washed with water and the product which separates at this point is of sufllcient purity for use as a yarn conditioning agent. The product is a mixture of amides having the general formula:

- one-H,

41H H: I

wherein R represents'a long-chain alkyl group.

Example 4 177 grams of diiurfurylamine is heated to a temperature of 100-150 C. in a flask fitted with a condenser. 110. grams of acetic anhydride is added slowlyand the reaction permitted to proceed for a period oi one hour. When the reaction is completed any excessacetic acid is distilled 0d and the product, which i a heavy, viscous oil is distilled underreduced pressure. The product is N-di-furfurylacetamide having the graphic formula HC-CH 111 g-cn, I

Following the procedure above described various other furfuryl and diiuriuryl amine derivatives may be prepared among which may be mentioned the following.

- N-butyryl furfuryl ethyl amine N-propionyl-furfuryl ethyl amine N-acetyl furfuryl ethyl amine N-acetyl furfuryl butyl amine N-acetyl furfuryl cetyl amine N-acetyl furfuryl lauryl amine N-acetyl furfuryl phenyl amine N-acetyl furfuryl-beta-hydroxyethylamine and acetate I N-acetyl tetrahydrofurfuryl methylamine N-acetyl tetrahydrofurfuryl ethylamine N-acetyl tetrahydrofurfuryl butyrylamine N-acetyl tetrahydrofurfuryl cyclohexylamine N-acetyl tetrahydrofurfuryl naphthenylamine N-acetyl tetrahydrofurfuryl laurylamine N -acetyl tetrahydrofuriuryl cetylamine N-lactyl tetrahydrofurfuryl cetylamine N-butyryl tetrahydrofurfuryl laurylamine N-valeryl tetrahydrofurfuryl decylamine N-valeryl tetrahydrofurfuryl cyclohexylamine YARN Lusnrcsrmc AND ANTI-STATIC TREATMENT Our invention will be more readily understood by reference to the following specific examples of typical yarn treating compositions whichmay be applied to yarns, filaments or fibers to condition them for various textile operations such as knitting, weaving, spinning and the like.

Example 5 N-difurfurylstearylamide is applied to textile materials (silk, wool, cotton. nylon, viscose, cellulose acetate, Vinyon, etc.) by means of a bath, wick, roller, spray, etc., to facilitate their imitting, weaving, spinning, and the like. If the yarn is intended primarily for knitting the amount of conditioning liquid applied may vary from 2 to 25% by weight of the yarn. If the yarnis intended primarily for weaving the amount of con- 1 ditioning liquid applied may vary between i and 5% of the weight of the yarn.

v Example 6 I I N=diiuriuryllaurylamide is applied to textile materials (cellulose acetate, W001, nylon, Vinyon,

cotton, viscose, etc;) from a benzene solution as;

in Example 5. The benzene is thenremoved by passing the materials through a suitable'drying cabinet. As in Example 5, the amount of the composition applied to the textile material will be determined-by the use to-which the yamfis to be put-or the particular textile operation it is desired to facilitate.

I Example 7 A conditioning liquid is made up as follows:

Parts Olive oil 99- 1 N-ditetrahydrofuriuryl oleylamide 1-99 This is applied to textile materials such as silk, wool, cellulose acetate and the like as described in Example 5. Cellulose acetate filaments or fibers treated as described above are quite soft and pliable and give improved results in various textile operations such as weaving, knitting and spinning.

Other examples of yarn conditioning composi- Q such yarns and render them amenable to a variety of textile operations such as kniting, weaving, spinning and the like are the following.

N-diturturylbutyrylamide l Blown sperm nil 60 Example 15 .Parts N-diiurfuryl pahnitylamide; 1-30 Mineral oil 98-70 Example 16.

. Parts Mineral oil 30 N-tetrahydrolurfurylphenylsulfoacetylamide I 30 Blown neats-foot oll' a 30 Oleyl alcohol Tetrahydrofuriuryltetrahydrofuroate 5 Ethanolamine Mineral Oleic a Example 17 70-50 Oleic a l-25 N-difurfurylacetylamide 29-25 Example 18 '5? Mineral nil 25 Olive oil (eladlnized) 50 Diiurfurylamine stearate yl stearate Example 19 Example Parts 20 10 l0 10 I 3 Water 7 N-difurfurylstearylamide 10 Example 21 Beta-'methoxyethyladipate Blown neats-foot oil Sulfonated olive oil Mineral nil Oleic nod A 20% solution of cellulose acetate in acetone .in which is incorporated l-25% by weight of the cellulose acetate of N-furfurylbutyloleylamide is extruded through fine-orifices into an evaporative atmosphere. Theiilaments thus produced are wound, or twisted and wound. Yarns produccd from filaments thus prepared are pliable and suitable for knitting.

While we have chosen to illustrate our invenby reference to compositions designed primarily for the lubrication, softening, and anti-static conditioning of textile yarns to adapt them for various operations such as knitting, weaving, 4

is spinning .and the like. the compounds which Example 8 Parts N-furfurylnaphthenylamide 75-99 Beta-methoxyethyl succinate 25- 1 Example 9 Parts N-tetrahydrofurfuryl palmitylamide 75-99 Tetrahydroiurfuryl formal 25- 1 Example 10 Parts N-furfurylcetyl acetylamide 1-99 Blown olive oil 99- 1 Example- 11 Parts N-tetrahydrofurfurylcyclohexylstearylamide 1-40 Neats-ioot nil 99-60 Example 12 Parts N-furfuryltetrahydrofurfurylabietyl- V amide 7 1-50 Blown neats-foot 011-, 99-50 Example 13 p Parts N-ethylfurfuryl ceretylamide l-99 j Sperm oil 99- 1 Example 14 Parts Glycerylacetone acetate 10 Butyl' stearaf 20 contribute these valuable properties to yam treating compositions may also be employed as emulsifying, wetting, and dispersing agents, dye assistants, soaps and for other purposes in which a surface-active agent is required. However, such compounds find their most valuable application in the conditioning of textile yarns, particularly those composed of or containing cellulose organic acid esters such as cellulose acetate.

cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, as well as other cellulosic materials such as viscose, cellulose ethers and the like.

The particular method of application of the yarn treating compositions of our invention to the yarn will depend largely upon the nature of the yarn and the use for. which it is intended. In general, the compositions may be applied by any of the standard procedures such as roll, wick,

bath. or spray application. If the yarnls in continuousfilament form, compositions may bespplied just as the yarnemerges from the spinning cabinet, or while passing from package to package. Likewise, the lubricant may be applied during twisting, winding, crepeing or similar operations. In the case of cutstaple fibers-the compositions may be conveniently applied in the form Parts Parts Parts able anti-static properties to yarns, particularly of an emulsion bath or spray. preferably after any desired special treatment of the yarn such as crimping or the like. In some cases, the lubricating, softening and anti-static agent mayv be added to the spinning solution from which the yarn is to be spun.

The amount of the compositions applied will, in general, depend upon the purpose for which the yarn is to be used. For example, if the yarn ples,- such compositions may contain other lubri-- cating, softening, or anti-static agents to augment or supplement the effect of the primary in gredient and thus give the compositions added or improved properties. Likewise, solvents, nonsolvents, blending agents, co-solvents, emulsifying agents, dispersing agents and similar ingredients. may be added as circumstances may require to adaptthe compositions for specific uses. Similarly, various dyes or other coloring matter may be added to the compositions in case it is desired to permanently or fugitively tint the yarn undergoing treatment.

Although in the above examples we have referred to compositions containing specific proportions of the various ingredients, theamounts employed in any given case may vary. widely depending upon the particular purpose for which the composition is intended. For example, if it is desired to controlthe solvent, softening, or other specific action of the conditioning agent per se or of any other ingredient, the amount thereof may be adjustedin accordance with the desired action.

While we have found it convenient to describe our invention with particular reference to the treatment of yarns composed of or containing organic derivatives of cellulose, particularly eellulose acetate, the conditioning agents and compositions described herein are also applicable to the conditioning of many other types ofcellulose derivative yarns, such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, the celluloseethers such as ethyl, methyl and benzyl celluloses, Viscose and couprammonium cellulose, silk, wool, cotton and other natural and artificial materials.

The term "yarn as used herein and in the claims is to be understood as covering single fila- .ments, a plurality of filaments associated in the form of roving, threads and the like, either of high or low gtwist, composite threads or yarns composed of a mixture of natural and artificial filaments, composite threads iormedby twis together individual threads or strands of the same or difierent natural or artificial materials of the same or diflerent deniers, oreped or crimped yarns, and crimped or uncrimped cut staple fibers produced from natural or artificial ants, and spun yarn staple fibers.

The yarn conditioning methodsand compositions of our invention possess marLv outstanding advantages. The fundamental and distinguishing characteristic of the agents described herein is their ability to lubricate, soften and give valuproduced from such I those composed of or containing organic derivatives of cellulose such as cellulose acetate,

and to render them amenable to various textile operations. These agents are especially valuable in the anti-static treatment tive cut staple fibers. I

Among the various yarn treating compositions herein described, we have found that N-furiuryl palmityl amide, difurfuryl ricinoleyl amide and the mixed amides derived from naturallyoc-.

of cellulosev deriva curring oils by the procedure outlined in Example 3- are of outstanding value as lubricating and anti-static agents in the conditioning of textile .yarns', particularly those composed of 'or containing cellulose acetate andsimilarcellulose'organic derivatives.

What we claim and desire to secure by Letters Patent of the United States is:

1. The process of conditioning textile yarns comprising an organic derivative of celluloseto v render the yarn amenable to textile. operations. including knitting, weaving, spinning and the like which comprises applying thereto a lubricating and anti-static composition cont as its essential lubricating and anti-static component a carboxylic. amide having "the formula wherein Ac is an unsubstituted acyl group, R1 is a member of the group consisting of furfuryl and tetrahydrofurfuryl groups and R2 is a member of the group consisting of hydrogen, alkyl, hydroxyalkyl, furfuryl and tetrahydrofurfuryl groups.

2. The process of conditioning textile yarns comprising cellulose acetate to render the yarn amenable to textile operations including knit-- ting, weaving, spinning and the like which comprises applying thereto a lubricating and antistaticcomposition containing as itsessential lubricating and anti-static component a carboxylicamide having the formula 3. Textile yarns comprising organic derivatives of cellulose which are amenable to textile operations including knitting. weaving. spinning and the like, impregnated with a lubricating and anti-static composition containing as its essential lubricating and anti-static component a car boxylic amide having the formula wherein no is an unsubstituted acyl group, R1 is a member of the group consisting of furfuryl and tetrahydrofurfuryl groups and R2 is a member of the group consisting of hydrogen, alkyl, hydroualkyl, furfuryl and tetrahydrofurfuryl groups.

4. Textile yarns comprising cellulose" acetate Ac-N which are amenable to textile operations includ-- .ing knitting, weaving, spinning and the like, im-

pregnated with a lubricating and anti-static composition contg as its essential lubricating and render the yarn amenable to textile operations anti-static component a. carboxylic amide having including knitting, weaving, spinning and the the formula. like whicli comprises applying the 'eto a lubri- R! eating and anti-static composition containing as V its essential lubricating and anti-static compo- 5 nent N-inrmryl palmitylamide. o B! 6; Textile yarns comprising cellulose acetate, 1 wherein A615 i n u d 3W1 groan R is whichiare amenable to textile operations includa member of the group oonsisting o! furiuryl and mg kmmngg Weavingspifmmg and the m tetrahydrofurguryl groups 93,334.13 5 member pregnated with a. lubricating and anti-static com- 0f the group consisting of hydrogen 1w hy positifln as essential dmxyalkfl, furfuryl ttr hydrof rf ryl and anti-static component N-Iurfuryl pelmityl groups. I amide- 5. The process of conditioning textile yams v JOSEPH B. mom. comprising an organic derivative of cellulose to 15 J8 G Emmy. 

